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I tried to reproduce the problem without success. Here is what I tried:

- install a fresh 2.6.1 sts
- added the dm server tooling to it via the extension install and restarted
- disabled the general sts 2.6 update site
- added the sts 2.7 milestone update site
- "check for updates"

This showed me two components available for an update: general sts and the dm server tooling, both for M2. And installing that update also succeeded.
I guess we need to figure out what is different in your setting. Did you do something different to update to M2?